Pet Friendly Holiday Rentals

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Pet Friendly Holiday Rentals

Pet Friendly Holiday Rentals in Tolland, MA

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There are 3 pet friendly holiday rentals in Tolland, and 158 more nearby. Need help to decide where to stay with your dog? You can browse the results below and filter by amenities to find the perfect spot. All pet policy information is guaranteed and there are no booking fees!

Pet Friendly Waterfront Oasis

Big Dogs Allowed

2+ Pets Allowed

Waterfront Oasis

4.9 Westhampton, MA

Waterfront Oasis Pet Policy

This 3-bedroom house in Westhampton allows 3 dogs of any size for an additional fee of $100 per pet, per stay. Cats are also welcome.

Big Dogs Allowed

Iconic Cabin in the Berkshires

3.0 Sandisfield, MA

Iconic Cabin in the Berkshires Pet Policy

This 6-bedroom cabin in Sandisfield allows 1 dog of any size for no additional fee. Cats may also be allowed by request, but pets are not permitted in the carpeted bedrooms.

Small Dogs Only

2+ Pets Allowed

Sweet Dreams Retreat

4.8 Sandisfield, MA

Sweet Dreams Retreat Pet Policy

This 1-bedroom vacation rental in Sandisfield allows 2 dogs under 20 lbs for an additional fee of $25 per pet, per stay. Breed restrictions apply. Sorry, no cats.

Big Dogs Allowed

2+ Pets Allowed

Stylish Mid-Century Modern Berkshires Cape

Stylish Mid-Century Modern Berkshires Cape Pet Policy

This 4-bedroom house in Lee allows 2 dogs of any size for an additional fee of $200 per pet, per stay. Sorry, no cats.

Big Dogs Allowed

2+ Pets Allowed

Fickle Fox Farm

Fickle Fox Farm Pet Policy

This 3-bedroom house in Canaan allows 3 dogs of any size for an additional fee of $150 per pet, per stay. Sorry, no cats.

Big Dogs Allowed

2+ Pets Allowed

The Dolly at Garfield House

The Dolly at Garfield House Pet Policy

This 1-bedroom vacation rental in Lee allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Garfield House

Garfield House Pet Policy

This 2-bedroom vacation rental in Lee allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

South Quarter House

5.0 Russell, MA

South Quarter House Pet Policy

This 3-bedroom vacation rental in Russell allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request. Pets are not allowed on the furniture and must be crated if left unattended.

Big Dogs Allowed

2+ Pets Allowed

Peace & Quiet on the Lake

Peace & Quiet on the Lake Pet Policy

Dogs of any size are allowed at this 2-bedroom house in Becket for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Garfield House Studio at 208

Garfield House Studio at 208 Pet Policy

This vacation rental in Lee allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Granby Retreat

Granby Retreat Pet Policy

This 6-bedroom vacation rental in Granby allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Cozy Monterey Chalet

5.0 Monterey, MA

Cozy Monterey Chalet Pet Policy

This 2-bedroom chalet in Monterey is pet friendly! Dogs of any size are allowed for an additional fee of $50 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance.

Big Dogs Allowed

2+ Pets Allowed

Lakeside Home Near Tanglewood

Lakeside Home Near Tanglewood Pet Policy

This 2-bedroom house in Lee allows dogs of any size for an additional fee of $200 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Nottingham Court

Nottingham Court Pet Policy

This 2-bedroom vacation rental in Becket allows dogs of any size for an additional fee of $75 per pet, per stay. All pets must be approved in advance. No cats or puppies.

Big Dogs Allowed

2+ Pets Allowed

5/3 House with Fireplace

5.0 New Marlborough, MA

5/3 House with Fireplace Pet Policy

This 5-bedroom vacation rental in New Marlborough allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Quaint Berkshire Cottage

4.7 New Marlborough, MA

Quaint Berkshire Cottage Pet Policy

This 1-bedroom vacation rental in New Marlborough allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Half Moon

4.8 Great Barrington, MA

Half Moon Pet Policy

This 4-bedroom house in Great Barrington allows dogs of any size for an additional fee of $150 per pet, per stay, plus a $300 refundable deposit. Cats may also be allowed by request, but all pets must be approved in advance.

Big Dogs Allowed

2+ Pets Allowed

Rabbit Run

4.9 Stockbridge, MA

Rabbit Run Pet Policy

This 3-bedroom vacation rental in Stockbridge allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request, but pets must be cleaned up after. Four-legged guests are not permitted on the beds or furniture.

Big Dogs Allowed

2+ Pets Allowed

Bright & Comfy Log Home

5.0 Great Barrington, MA

Bright & Comfy Log Home Pet Policy

Dogs of any size are allowed at this 5-bedroom vacation rental in Great Barrington for an additional fee of $150 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

3BR House with Fenced Yard

4.8 Washington, MA

3BR House with Fenced Yard Pet Policy

This 3-bedroom vacation rental in Washington allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request. The yard is fenced.

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Tolland, MA, US